Premium
Salicylaldimine Ruthenium Alkylidene Complexes: Metathesis Catalysts Tuned for Protic Solvents
Author(s) -
Binder Joseph B.,
Guzei Ilia A.,
Raines Ronald T.
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600264
Subject(s) - chemistry , carbene , ruthenium , metathesis , catalysis , ring opening metathesis polymerisation , ring closing metathesis , denticity , steric effects , salt metathesis reaction , combinatorial chemistry , ligand (biochemistry) , homogeneous catalysis , acyclic diene metathesis , organic chemistry , metal , polymerization , biochemistry , receptor , polymer
Tuning the electronic and steric environment of olefin metathesis catalysts with specialized ligands can adapt them to broader applications, including metathesis in aqueous solvents. Bidentate salicylaldimine ligands are known to stabilize ruthenium alkylidene complexes, as well as allow ring‐closing metathesis in protic media. Here, we report the synthesis and characterization of exceptionally robust olefin metathesis catalysts bearing both bidentate salicylaldimine and N‐heterocyclic carbene ligands, including a trimethylammonium‐functionalized complex adapted for polar solvents. NMR spectroscopy and X‐ray crystallographic analysis confirm the structures of the complexes. Although the N‐heterocyclic carbene–salicylaldimine ligand combination limits the activity of these catalysts in non‐polar solvents, this pairing enables efficient ring‐closing metathesis of both dienes and enynes in methanol and methanol/water mixtures under air.